Her major breakthrough came as she made her solo debut at the 2008 Edinburgh Festival Fringe with Pippa Evans and Other Lonely People, playing a number of different characters at a self-help group meeting. Evans received positive reviews from the press, with The Scotsman citing her as "wicked and dark, with few gimmicks".[4] She subsequently gained a nomination for Best Newcomer at the Edinburgh Comedy Awards, before performing the show at London's Soho Theatre for a limited season.

She returned to the Edinburgh Festival Fringe in 2009 with another show titled Pippa Evans: Your Evening's Entertainment, a variety show for an imagined audience of conference delegates where Evans plays all the characters. In an interview with The Scotsman, Evans revealed "I was brought up with old time music halls and doing pantos in church halls... it was a big part of my background that always appealed to me".[7] The show was again warmly received but it was the character of Loretta Maine which critics highlighted unequivocally.[8][9][10] In November 2009 she curated and hosted Pippa's Old Time New Time Music Hall at the Canal Cafe Theatre, introducing audiences to her contemporaries Angelos Epithemiou, the Penny Dreadfuls and Wilfredo in a satire on the tradition of music hall.[11]

In 2010 she presented an entire show at the Fringe as Maine in I'm Not Drunk, I Just Need To Talk To You. The Independent's critic observed "Maine belongs to a recognizable stable of bitter songstresses and swigs on a screw-topped bottle of wine, while spewing out her vitriol any which way",[12] while the comedy industry website Chortle noted that "Psycho-intense singer-songwriter Loretta Maine makes Courtney Love look well-balanced. This pill-popping, booze-abusing, bunny-boiling car-crash of a rock star has been the most memorable creation of talented character comic Pippa Evans to date".[13]